tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,7R]-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Base Information

Chemical Name:tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,7R]-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate
CAS No.:171190-03-7
Molecular Formula:C₄₂H₆₂O₁₅
Molecular Weight:806.945
Hs Code.:

tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,7R]-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Synonyms:tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,7R]-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

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Chemical Property of tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,7R]-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,7R]-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

There total 12 articles about tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,7R]-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

: 925453-76-5
tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,7R]-6-acetoxy-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

: 171190-03-7
tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,7R]-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 1h;
DOI:10.1002/chem.200601212

Reference yield:

: tri-tert-butyl [1S,1(2E,4S,5R),3S,4S,5R,6R,7R]-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-1-(4-hydroxy-5-methyl-6-phenyl-2-hexenyl)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

: 171190-03-7
tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,7R]-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 0 °C

2: Bu₃SnH; 2,2'-azobisisobutyronitrile / benzene / 1 h / Heating

3: 102 mg / NaHCO₃; KF; aq. H₂O₂ / tetrahydrofuran; methanol / 24 h

4: 95 percent / Pd(OH)2/carbon / ethyl acetate / 13 h / 760 Torr

5: 62 percent / Bu₃P / tetrahydrofuran / 0.5 h

6: 98 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

7: 93 percent / aq. H₂O₂ / tetrahydrofuran / 4 h / 20 °C

8: 80 percent / potassium carbonate / methanol / 1 h / 20 °C

With dmap; potassium fluoride; 2,2'-azobis(isobutyronitrile); tributylphosphine; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; palladium dihydroxide; pyrographite; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; benzene; 3: Tamao oxidation;
DOI:10.1002/chem.200601212

Reference yield:

: 925453-70-9
6-benzyloxy-7-tert-butoxycarbonyloxy-1-{2-[2,2-dimethyl-5-(1-methyl-2-phenyl-ethyl)-[1,2]oxasilolan-4-yl]-ethyl}-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

: 171190-03-7
tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,7R]-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 102 mg / NaHCO₃; KF; aq. H₂O₂ / tetrahydrofuran; methanol / 24 h

2: 95 percent / Pd(OH)2/carbon / ethyl acetate / 13 h / 760 Torr

3: 62 percent / Bu₃P / tetrahydrofuran / 0.5 h

4: 98 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

5: 93 percent / aq. H₂O₂ / tetrahydrofuran / 4 h / 20 °C

6: 80 percent / potassium carbonate / methanol / 1 h / 20 °C

With dmap; potassium fluoride; tributylphosphine; dihydrogen peroxide; sodium hydrogencarbonate; potassium carbonate; palladium dihydroxide; pyrographite; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 1: Tamao oxidation;
DOI:10.1002/chem.200601212